500 Days of Castiel Milton
by There-Are-Things-I-Can't-Say
Summary: Dean Winchester lives an average life in a job that he doesn't like. But when his boss hires a new assistant, it seems like his luck is going to change for the better. Completely AU Destiel don't like please don't read : Warnings for swearing I guess but T for the time being... Enjoy! xx
1. Prologue and Day one

**Disclaimer: I own no rights to either Supernatural or 500 Days of Summer, I'm gonna go to my box and cry now **

**A/N: Hi so I have like four stories I needed to update but I watched 500 Days of Summer and I just kept on picturing Dean and Castiel in those roles :') I don't think I've seen a fic like this but if anybody has please tell me because I'd hate to steal anyone's idea or plot Anywho I really appreciate reviews and criticism It probably wont exactly follow the movie story and I apologise if any is ooc :D**

**Enjoy! **

**Emm xx**

**Prologue**

**Day 290**

_**His life was over. It wasn't even an understatement; Dean Winchester was well and truly fucked. It hadn't even been a year and his world had turned upside down, inside out; been broken apart and taped back together just to be split into pieces once again. **_

_**He closed his eyes and images of dark blue orbs and a mess of untidy black hair invaded his mind everywhere he went. He had known something was off but he hadn't dared himself to think anymore of it. He had never been this happy with somebody, never allowed himself to immerse his heart and soul into one relationship.**_

"_**I think we should stop seeing each other."**_

_**Dean looked up from his cheeseburger in shock. Of all the words he had expected to come out of his partner's mouth, never in all of the world was it those eight. **_

_**Shit.**_

**DAY ONE**

"**Dude, hurry up!"**

**Dean called up the stairs to his sixteen year old brother. Sam was a demon in the morning and if he didn't move his ass soon then he would miss first period and Dean was not signing another imaginary dentist slip. **

"**Alright, alright. Geez." **

**Sam came clattering down into the kitchen, hopping on one foot in order to pull his sock on properly. He had grown again over the summer Dean noticed as he glanced upwards. Despite the four year age difference Sam towered over his older brother. He chucked the floppy haired teen his satchel and they wandered outside to Dean's prize posessesion, his impala. Though Sam had his licence as well, there was no way the idiot was ever sitting in his baby's driver seat. **

"**You won't forget about Lisa's engagement party this weekend right?" **

**Sam asked as they pulled up outside his ridiculously fancy scholarship earned private school. He unclipped his seatbelt and to fix Dean with an unnerving stare. **

"**Right?"**

**Dean rolled his eyes but was unable to keep the smile off of his face. Sam was an overeager puppy in a vessel; and Dean loved Lisa, he was truly happy that she had found somebody to spend her life with. They weren't a good couple he could see that now, but she was still his best friend, stayed with him while he tried to find himself and always would be there. **

"**Yeah yeah Sammy, I won't forget I promise. Now scoot, go and learn smart things to put inside of your abnormally large head." **

**Sam shot Dean the two finger salute as he clambered out of the car with the same gracelessness he applied to the majority of tasks and jogged over to a group of friends that were waiting for him.**

* * *

_**Other mother day, seriously? **_

**Dean thought as he tapped his pen against his folder absent minded. The meeting had only been going on for twenty minutes and he was bored out of his mind. He had never wanted to go into the greeting card business but there was no way he could juggle studying for a mechanics degree whilst working here and Ellen's bar in the evening. His main priority was to make sure Sam had everything he needed, that was all that mattered. **

"**Dude where'd you get to last night?"**

**Ash, Dean's colleague and sometimes drinking buddy was muttering to him out of the corner of his mouth. He was the graphics designer for the company and had been the one to get the job cemented for Dean.**

"**Oh yeah sorry Sam needed me to come home."**

**Ash opened his mouth to reply but was interrupted when the door opened and the newcomer stepped into the conference room. Dean's eyes snapped up to see a man walk over to their boss Crowley and whispered into the Englishman's ear . Crowley straightened up and turned to his employees. **

"**I'm sorry but there's something I must take care of. Oh uh yes, everybody this is my new assistant Castiel Milton from uh-"**

"**Massachusetts" **

**The guy, Castiel supplied helpfully. Something heavy started to curl in Dean's stomach as the gravely voice reached his ears. Crowley nodded and left the room leaving Castiel standing in front of twenty strangers. **

"**So uh it was nice to meet you all." The dark haired man tugged on the edge of the ugly trench coat that he was wearing over his suit. He picked up Crowley's empty coffee mug, and made to leave. His gaze swept over the bored faces before eyes landing on Dean. The look was heated and made the hairs on the back of Dean's neck stand on end as if they had been electric shocked. **

**Damn he was screwed. **

**A/N: Okay first chapter is done Good? Bad? I'd love to know what you think it makes me want to write more :D like I said crit is welcome ;) xx**


	2. Day one cont and Day two

**A/N: Hi I'm baaackk :D I don't know if people are reading this but oh well I'm really invested in writing this atm :D **

**Astermoose: Aww Thank you :D you my have just inflated my ego lol. Hehe I know I watched it the other day and I was the same thinking about them the whole time Ooooh Pie yum yum :D**

**Eleni: Aw well thank you I'm so glad you like it :D Hehe I'm not promising anything but maybe :P The ending of the movie broke me into pieces and I don't normally like films like that ;) So who knows heehee**

**Enjoy!**

**Emm xx**

**DAY ONE –**(Cont)

**Dean had managed to avoid human contact with Castiel for most of the day. He had eaten lunch with Ash and the creepy dude Chuck from PR now he was ready to go home and sink into his bed for the night. **

**Snapping the headphones of his iPod up over his ears, he waved briefly at the few remaining workers and pressed the button of the elevator, tapping his foot in rhythm to the bass guitar in the song. The metal doors opened with a bing and Dean went to step in but stopped when he realised there was a body in the way of the space he had meant to occupy. **

**Castiel was standing inside of the device, bright blue eyes focused on Dean and his mouth quirked upwards in a small smile. Dean nodded his head in greeting and moved to stand next to the man; fixing his eyes on anywhere but the attractive assistant. Unfortunately the interior was downright ugly and he found himself risking little glances to the side. The third time it happened, he caught Castiel's amused expression and felt a slight blush spreading throughout his face. **

"**What are you listening to?"**

**Castiel enquired slightly louder than necessary so that Dean could hear the question. The elder Winchester lifted the headphone off of the closest ear and shuffled his feet uncomfortably. This damn elevator ride was taking forever. **

"**Uh, Led Zeppelin"**

**At Castiel's blank look, Dean let his jaw drop open in slight surprise. **

"**Dude, you being serious? Stairway to Heaven, Sick again, Poor Tom?"**

**All Dean got in return was a confused head tilt. "I'm sorry Dean but I am not familiar with this music."**

"**I- What.. H-How do you know my name is Dean?" **

**The elevator grounded to a halt before he could find out how Castiel knew who he was without properly being introduced. Castiel shot him another half smile as he stepped out. **

"**I have my sources, good night Dean." **

**DAY TWO**

"**So you know that new dude?" Ash was sitting on his desk as Dean came in the next morning. Dean sighed but didn't attempt to move the other man, he knew him too well. **

"**Castiel? What about him?"**

**Ash glanced around the office floor before leaning forwards and dropping his voice to a stage whisper. **

"**Chuck told me that Meg came onto Castiel yesterday in the copy room and he totally blew her off, he's gotta be batting for our team."**

**Dean rolled his eyes and shoved at Ash's elbow so that he could sit down in his chair. "You shouldn't make assumptions before you know the guy. Maybe he has a sixth sense where he can tell whether or not certain people are crazy bitches from five miles off." **

"**Whatever dude. I mean, yeah each to their own and all that shit but I'd definitely go for it with Meg if I were him."**

"**Well you aren't him." Dean's tone came out colder then he had intended to and he blinked, slightly confused with himself for the sudden streak of defensiveness that had appeared for a man he had only met one day ago. **

**Ash hopped effortlessly off of the desk and moved round to his own cubicle opposite of Dean's own one. As Dean sorted out his papers that the other man had messed up, he looked up and noticed that Castiel was watching him from across the room intently. He raised a hand in Castiel's direction and tried not to think about what it meant when his heart flip flopped pathetically at the nod he received in return.**

* * *

"**Why are you smiling like that?" Sam's nose wrinkled as he looked up from his homework at his older brother. **

**Dean turned away from the stove in time to the music playing loudly from the stereo and thrusting the wooden spoon in Sam's direction.**

"**Taste." He ordered and raised an eyebrow as Sam obediently dabbed a finger in the pasta sauce. "Smiling like what? I'm not smiling like anything."**

"**You look like a goof." Sam stated bluntly and grinned all of a sudden as if a light bulb had gone off. "Aw Dean have you met someone?" **

"**What? NO!"**

"**Oh my God you have!" Sam pushed away his textbook impatiently and leaned across the table, attention intently on his brother. "Who is it? Someone at work I'm guessing. Tell me"**

**Dean rolled his eyes at his nosy brother's persistence but couldn't help smiling a little as he met the large hazel orbs doing their best puppy expression. **

"**Alright fine there might be somebody I'm interested in."**

"**Ha I knew it!" Sam pumped a fist in triumph, ignoring the elder Winchester sticking his tongue out childishly at him. **

"**But I don't even know if he likes dudes let alone if he's available."**

**Dean had been hurt too many times that he was definitely on the scale of careful when it came to new people and maintaining even a simple friendship. Sam knew this but all he wanted was that Dean could find a little happiness in his life, God knows he'd been dealt the short straw often enough. **

**A/N: Okay second chapter done I'm having a lot of fun with this story I hope you guys like it xxx**


	3. Day three and Day four

**A/N: Oh hi I'm not sure if anyone's reading this but I'm having a lot of fun writing it :P :P Thank you for the follows and reviews and whatnot ;) **

**Enjoy!**

**Emm xx**

**DAY THREE**

"**So I haven't heard from you in like a week, I thought maybe you'd fallen down the toilet or something." Lisa knocked her shoulder against Dean's as they strolled down the street through the early morning crowds of people rushing to get to work. Dean rolled his eyes as he took a sip of the scalding hot coffee he was holding. **

"**Yeah I been kinda busy y'know, Sam has exams coming up and I've been helping him study when I'm not at work or the bar."**

"**Oh cut the crap Winchester! I know you think I've been over obsessing about the wedding and that's why you've been dodging my calls."**

"**Lis you haven't had the engagement party yet and you've already narrowed it down to three colour schemes for the big day."**

**Lisa glared playfully at her best friend and stole the cup out of his hands so that she could drink from it.**

"**I like to be prepared there isn't a ban on that you know. Speaking of which, which floozy are you bringing on Saturday? Please tell me it isn't that crazy superskank from the bar?"**

"**I have no idea who you are referring to, Miss Braeden. But alas I will be flying solo."**

**They came to a stop outside of Dean's company building and Lisa handed back his coffee whilst fixing him with a stern glare. **

"**You're up to something Dean I know you too well."**

**Dean smiled and shot her a brief wink before disappearing through the entry doors, leaving Lisa standing on the street staring at his retreating form.**

"**Good morning Dean."**

"**Huh what? Oh hey Cass." **

**From his seat Dean could see the man's form freeze at the new nickname he had suddenly acquired but as quickly as it had hit Castiel snapped out of it and was shrugging his coat onto the back of his own chair. **

"**How was your night?" **

" **Uh fine… And yours?"**

**Castiel's lips quirked upwards in that little half smile that Dean had seen in his dreams since he'd been graced with it the other day in the elevator and his eyes adopted a slightly glazed surface.**

"**It was good."**

**Dean's eyebrow escalated up into his hairline on its own accord. He knew that look all too well but never had it made him as uncomfortable as it did right at that moment. He cleared his throat unnecessarily and busied himself with straightening the folders that miraculously turn ed up on his desk.**

"**Uh that's great man."**

"**Are you okay Dean?"**

**The hazel eyed man glanced up again to see Castiel watching him intently, concern now etched on his features as his eyes followed Dean's movement. Dean forced a smile onto his face, he had perfected doing that over the years so that he wouldn't look like a constipated rat. **

"**Yeah Cass, I'm fine."**

* * *

**DAY FOUR**

"**Hey!" **

**Dean blinked as a dishcloth was flicked in his face and Jo was standing in front of him, frowning. **

"**What?"**

"**You're meant to be working here not killing time until the apocalypse strikes." **

**Dean sighed and grabbed the cloth from the blonde's hand, wiping down the bar counter obediently. Even though it was creeping close to midnight there were still more than two dozen patrons lounging round Ellen's Bar. As he finished cleaning up the spilled scotch off of the wooden surface he realised that Jo hadn't moved from her spot.**

"**Need something?" **

"**Yeah you doof, drinks. The couple over there want a whiskey on the rocks and a beer and they want it like an hour ago."**

**Dean turned his head to the two o clock position to catch a glimpse of the people Jo was talking about then double… No, triple taked at the sight that greeted him. **

**Castiel was sitting at a booth with a blond haired man. The man was leaning over the table and playing with Cass's fingers one by one whilst the raven haired smiled softly, his eyes dancing in the soft ambient of the bar's lighting. **

**Dean's stomach lurched and he swayed unsteady on his feet, thanking whatever God there was that he was behind the bar that night and not serving tables. **

"**Dean?"**

**Jo's tone had switched from impatience to sisterly concern in a matter of seconds as the native Kansan's face paled significantly. **

**Dean fumbled for the opening hatch that had been installed and walked robotically into the main area of the bar, hoping that he hadn't been seen. A quick peek told him that Cass was stil unaware of his surroundings other than that moment with that man and Dean had to get out of there as fast as he could. **

"**I- Uh I just remembered I gotta pick Sam up from the uh… the library."**

**He snatched his jacket and keys up from where he had dropped them when he started his shift and dashed towards the door. **

"**The library?! Dean it's midnight!" **

**Ingnoring's Jo's yells after him he slipped outside of the building and all but ran down the street until he was at least three blocks away from the bar. **

**Sliding down the wall of a closed boutique, Dean landed gracelessly onto the concrete and dropped his head into his hands. Feeling something damp on his palm he pulled away to see water smeared on them. He hadn't even noticed that he had been crying. He sighed sadly and scrubbed at his eyes in resignation.**

_**Shit **_**he thought to himself, opting to whack his head against the shop's wall instead. **_**I've got it bad for Cass.**_

* * *

**A/N: So end chapter three I'd love to know what you think? I'm not sure whether to continue or not :') xx**


	4. Day five

**A/N: FML! Hello I'm still alive I'm so sorry I've been MIA Thank you for the reviews and follows :') Between packing to go to uni in four weeks and holiday in two weeks I haven't had the time or energy to update But I have the weekend to myself so I might be able to write more then hopefully :') **

**Enjoy!**

**Emm xx**

**DAY FIVE**

**Lisa and Jason's engagement party was in full swing by the time that Dean had arrived. He found Sam in the middle of the dance floor showing off some questionable moves to a group of giggling girls and even some boys and rolled his eyes fondly at the dork as he sauntered off to find a beer; nodding at a few people that he recognised. **

"**Dean!" Lisa came flying towards him as soon as he had gotten a drink and sat down at a table by the door. She was pulling a petite woman by the hand and laughing wildly. The girl that Dean had never met before smiled shyly when he raised his beer bottle in greeting.**

"**Great party, Lis." He grinned and took a swig of the alcoholic beverage whilst casting an eye out on the dozens of well wishers. **

"**Oh I know, looks like Sam is enjoying it. Anyway, Dean this is Anna. Anna's going to be my maid in honour."**

**Dean raised an eyebrow and smiled again. "Oh really? Did she blackmail you as well?"**

**Anna laughed in reply as Lisa slapped her friend's head playfully and pretended to storm off in a huff. **

"**No, actually I was very honoured when she asked me." Anna arranged her floral dress carefully as she perched on the wire chair opposite Dean. She was extremely pretty with dyed dark red hair and large green eyes, totally the kind of girl that younger Dean would go after. **

"**I'm sure you were." He was just about to ask how she knew Lisa when the last person he had expected and wanted to see wandered over to the pair. **

"**Anna, the car is- Dean?"**

**Dean hoped that his gulp wasn't audible or visible to the two adults who were watching him with the same mixed expression of confusion and curiosity. **

"**Hi Cass, didn't think I'd see you here!" **

**His tone was way too chirpy and he cursed internally as Castiel's brow wrinkled and a large rough hand settled on Anna's shoulder. **

"**I'll go get us some drinks shall I?" Anna jumped up quickly and smiled reassuringly at Castiel. "I'll be back in a few, okay?" **

**Castiel watched the girl until she disappeared from view and then turned back to face Dean who was suddenly shuffling uncomfortably. **

"**So uh-"**

"**Anna is my sister." The words flew out of Castiel's mouth before he could stop them and he sat down heavily. **

"**Yeah, cool dude."Dean was invested in picking the label off of his bottle and was stunned when a hand reached out and placed itself over his nervously. He stared at the obvious contact until Castiel cleared his throat in embarrassment and pulled away.**

"**I'm sorry, your fidgeting was making me agitated. I'm quite a nervy person. My college roommates used to call me anal boy."**

**The glug of beer that Dean had taken to cool himself down was spat out instantly.**

"**Not because… It was just because I had to have everything quiet and neat while I was studying."Castiel amended like he had only just realised the innuendo of what he had just said**

"**Right, yeah I got that." They fell into an awkward silence again until Sam came bounding up to his brother all gangly limbs and gleeful expression. **

"**Dean! This party is awesome! Oh, hello."**

**His happiness was catchy and Dean found himself chuckling a little as he introduced the two. **

"**Your name is seriously Castiel? Dude, that's an amazing name!" Sam gushed and Dean could tell that the man was trying to bite back an embarrassed laugh. **

"**Yes, my parents have a fascination with celestial objects; I am named after the angel of Thursday."**

"**Better than being known as anal boy." Dean muttered under his breath, but by the way Sam was looking at him it was obvious that he had heard. **

"**Well anyway, it was good to meet you. Dean always talks about his colleagues. Hey, you haven't by any chance seen him being ridiculously flirty with anyone have you?"**

**Castiel's eyebrow rose as he glanced back and forth between the two brothers. "Not that I have noticed."**

"**Damn, that's a shame. Guess I'll have to keep prying then." Sam smiled radiantly and with a wave of his freakishly massive hand he ran off back to the dance floor. **

"**Sorry about that my brother can be a bit full on sometimes."**

"**It's fine Dean." The slight smile had returned and for some reason it made Dean's fingertips tingle. "Sam seems very nice. My brothers are not so friendly."**

**Dean laughed and leant back in his seat, closing his eyes for a moment as he let the warm sun caress his face. When he opened them again, Castiel was looking at him unblinkingly and with a tensed jaw. **

"**You okay man?" **

"**Of course. I'm sorry I have to go and find Anna now."**

**Without another word, he rose upwards and walked away through the crowds of people, leaving Dean still sitting there with an incredibly strange feeling flowing through his veins. **

**A/N: So I'm tired.. Which isn't an excuse for how shit/boring/wordy this is I'm sorry Hugs? Or cookies either work hehehehe xxx**


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